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Atrop-abyssomicin C
''Atrop''-abyssomicin C is polycyclic polyketide-type natural product that is the atropisomer of abyssomicin C. It is a spirotetronate that belongs to the class of tetronate antibiotics, which includes compounds such as tetronomycin, agglomerin, and chlorothricin. In 2006, the Nicolaou group discovered ''atrop''-abyssomicin C while working on the total synthesis of abyssomicin C. Then in 2007, Süssmuth and co-workers isolated ''atrop''-abyssomicin C from ''Verrucosispora maris'' AB-18-032, a marine actinomycete found in sediment of the Japanese sea. They found that ''atrop''-abyssomicin C was the major metabolite produced by this strain, while abyssomicin C was a minor product. The molecule displays antibacterial activity by inhibiting the enzyme PabB (4-amino-4-deoxychorismate synthase), thereby depleting the biosynthesis of ''p''-aminobenzoate.
==Structure ==
''Atrop''-abyssomicin C has a complex, yet intriguing structural topography. The compound contains a oxabicyclo()octane system fused to the tetronate moiety. The 11-membered macrocyclic ring carries an α,β-unsaturated ketone that was proposed to be the reactive center. Despite being a strained macrocycle, there exist an atropisomer, abyssomicin C. The atropisomerism arise due to a structural deviation in the α,β-unsaturated ketone region of the molecule. The orientation of the carbonyl in ''atrop''-abyssomicin C is cisoid, whereas the conformation in abyssomicin C is transoid. The enone moiety of ''atrop''-abyssomicin C has a higher degree of the conjugation, which makes it a more active Michael acceptor.〔
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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